Singapore’s multi-racial and multilingual vibrancy has contributed to the evolution of its language ecology. The all-time high of 71% of ethnic Chinese students in the first year of school coming from English-speaking homes, indicates that the last frontier of mother tongue has been usurped by English. Under such circumstances, it is useful to retrospectively examine the situation of the Chinese dialects in the past and the present, and envision the future development of Chinese dialects in Singapore. This chapter analyses the historical and social contexts that have shaped the development of Chinese dialects in Singapore. It also analyses survey findings to evaluate the use of dialects, and attitude towards dialects, among Chinese Singaporeans. Despite the less favourable perceptions associated with dialect use, portrayed by policy makers, the findings indicate that respondents remain positive towards the use of dialects among family members and in heartland locations. Based on the positive attitudes and inclinations to equate their sub-ethnic identity with dialect use, there is still some impetus for the retention of Chinese dialects in Singapore for pragmatic and functional uses. However, the survival of Chinese dialects will face challenges with the gradual decrease in active speakers, especially if individuals, community groups and official heritage boards do not actively preserve, revive or curate such languages through collective efforts.